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epoxyqueuosine (M2MDB003576)

Record Information
Version2.0
Creation Date2012-10-10 12:21:06 -0600
Update Date2015-06-03 17:26:07 -0600
Secondary Accession Numbers
  • ECMDB23186
Identification
Name:epoxyqueuosine
DescriptionEpoxyqueuosine is an intermediate in queosine biosynthesis. Queuosine is an important 7-deazapurine-modified nucleoside that is present in certain tRNAs in bacteria and most eukaryotes. Eposyqueosiine is a subsstrate for Epoxyqueuosine reductase catalyzes the final step in the de novo synthesis of queuosine, the anticodon loop modification found in tRNA(Asp), tRNA(Asn), tRNA(His), and tRNA(Tyr)
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms:
  • 2-amino-7-(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl-5-(3,4-dihydroxy-6-oxabicyclo3.1.0hexan-2-yl)aminomethyl-1H-pyrrolo2,3-dpyrimidin-4-one
Chemical Formula:C17H23N5O8
Weight:Average: 425.3932
Monoisotopic: 425.154662737
InChI Key:RRCFLRBBBFZLSB-MPMHWICOSA-N
InChI:InChI=1S/C17H23N5O8/c18-17-20-14-6(15(28)21-17)4(1-19-7-9(25)10(26)13-12(7)30-13)2-22(14)16-11(27)8(24)5(3-23)29-16/h2,5,7-13,16,19,23-27H,1,3H2,(H3,18,20,21,28)/t5-,7?,8-,9?,10?,11-,12?,13?,16-/m1/s1
CAS number:Not Available
IUPAC Name:4-[({7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-2-imino-1H,2H,7H-pyrrolo[2,3-d]pyrimidin-5-yl}methyl)amino]-6-oxabicyclo[3.1.0]hexane-2,3-diol
Traditional IUPAC Name:4-[({7-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-2-imino-1H-pyrrolo[2,3-d]pyrimidin-5-yl}methyl)amino]-6-oxabicyclo[3.1.0]hexane-2,3-diol
SMILES:[H]C12OC1([H])C([H])(NCC1=CN(C3=C1C(O)=NC(=N)N3)[C@]1([H])O[C@]([H])(CO)[C@@]([H])(O)[C@@]1([H])O)C([H])(O)C2([H])O
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrrolopyrimidine nucleosides and nucleotides. These are nucleoside derivatives containing a ribose derivative which is n-glycosylated to a pyrrolopyrimidine. Also called deazapurine nucleosides, they are analogs of purine nucleosides with the N atom of the purine being replaced by a C atom at position 7.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrrolopyrimidine nucleosides and nucleotides
Sub ClassNot Available
Direct ParentPyrrolopyrimidine nucleosides and nucleotides
Alternative Parents
Substituents
  • Pyrrolopyrimidine ribonucleoside
  • Glycosyl compound
  • N-glycosyl compound
  • Pentose monosaccharide
  • Pyrrolo[2,3-d]pyrimidine
  • Pyrrolopyrimidine
  • Aminopyrimidine
  • Pyrimidone
  • Aralkylamine
  • Substituted pyrrole
  • Monosaccharide
  • Oxane
  • Pyrimidine
  • Heteroaromatic compound
  • Vinylogous amide
  • Cyclic alcohol
  • Tetrahydrofuran
  • Pyrrole
  • 1,2-aminoalcohol
  • Secondary alcohol
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Dialkyl ether
  • Secondary aliphatic amine
  • Oxirane
  • Ether
  • Secondary amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxide
  • Organopnictogen compound
  • Primary alcohol
  • Primary amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Physical Properties
State:Not Available
Charge:2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility11.2 g/LALOGPS
logP-2ALOGPS
logP-3.5ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)8.12ChemAxon
pKa (Strongest Basic)7.19ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area208.34 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity108.67 m³·mol⁻¹ChemAxon
Polarizability41.18 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
S-adenosyl-L-methionine + 7-Aminomethyl-7-deazaguanosine > L-Methionine + Adenine + epoxyqueuosine
7-aminomethyl-7-deazaguanosine34 in tRNA + S-adenosyl-L-methionine > Hydrogen ion + L-Methionine + Adenine + epoxyqueuosine
SMPDB Pathways:
preQ0 metabolismPW001893 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_5_46) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-0190500000-4bf2c623937e408d8c12View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01r6-1390000000-161e99fd241fb8a0b070View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-02bf-2970000000-f7be51e3d3034bcffb3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dl-0352900000-a85259aa6433a85435aeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0391000000-676e48ba02c1cf255bc7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0960000000-4b96461d04f006aa653aView in MoNA
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableView in JSpectraViewer
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI IDNot Available
HMDB IDNot Available
Pubchem Compound ID135783056
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. S-adenosylmethionine:tRNA ribosyltransferase-isomerase
General function:
Translation, ribosomal structure and biogenesis
Specific function:
Transfers and isomerizes the ribose moiety from AdoMet to the 7-aminomethyl group of 7-deazaguanine (preQ1-tRNA) to give epoxyqueuosine (oQ-tRNA)
Gene Name:
queA
Uniprot ID:
P0A7F9
Molecular weight:
39430
Reactions
S-adenosylmethionine + 7-aminomethyl-7-deazaguanosine = methionine + adenine + epoxyqueuosine.